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Synlett 1998; 1998(8): 859-860
DOI: 10.1055/s-1998-1816
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(4S)-4-[(1R)-1-Hydroxy-2-trifluoromethylpropenyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester: Highly Diastereoselective Synthesis and Palladium-Catalyzed Arylations

Sheng Peng* , Feng-Ling Qing, Yinlong Guo
  • *Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 20 00 32, P.R. China; Fax 86-21-64 16 61 28; E-mail: flq@pub.sioc.ac.cn
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Publication Date:
31 December 2000 (online)

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CF3-substituted allylic alcohol 2 was obtained in high diastereoselectivity from the Zn-Ag promoted Barbier-type reaction of 2-bromo-3,3,3-trifluoropropene with Garner aldehyde 1. Palladium-catalyzed arylation of 2 provided a novel way to elaborate the side-chain of α-amino acid derivatives containing a CF3 group.

Garner aldehyde - trifluoromethylated - Heck reaction